Dan O’Leary, Senior Director of Strategic Partnerships at Box: Scaling Success Through Partnerships

Scott Smith: All right.

Scott Smith: He is the senior director of partnerships at Box,…

Scott Smith: longtime Facebook Metamate and he has been building SAS partnerships and driving innovation at some really great companies for a while now. welcome to the podcast, Dan.

Dan O’Leary: Thank you so much,…

Dan O’Leary: Great to see you again, being one of the only other people at work that wore sandals other than me, which was always great, but great great to see you and…

Dan O’Leary: everyone today. I’m Yeah, as mentioned, other than working at Box Scott and I had a chance to build at the time what was called Facebook at work, workplace, maybe something different, but yeah, spent a lot of time in my career focusing on technology, partnerships, customer success, cool tech, and had a chance to do it with Scott and I’m super excited to spend some time with you today and share more about it. It’s going to be great.

Scott Smith: Yeah, cool. I love the idea of rehashing a little bit of our prior history together at building a product in a consumer company that was intended for work. you’re working for I don’t know smartest enterprise focused businesses.

Scott Smith: So, Why don’t we talk a little bit about what it was starting to build Meta workplace? I guess we actually changed the company name post while we were there, so I still have a hard time remembering it.

Dan O’Leary: Yeah. Yeah.

Scott Smith: What do you look back and think about when you think about workplacement

Dan O’Leary: Or at the time it was called Facebook at work. I have a bunch of great anecdotes, but one of my favorite is meeting with the CIO very early on when the product was still in stealth and he goes, ” guys, spent the last five years trying to get my employees off Facebook at work and here you are trying to bring it in.” I was like, “Okay, maybe we need to rename this thing. Better call the brand.” But it was super interesting. You joined before I did, Scott. And I had a chance to join the journey pretty early on before we had signed up any paying customers.

Dan O’Leary: I think before we launched taken out of stealth and at the time I think Facebook probably had a billion users just a billion now over three billion and there was just this incredible experiment to say what if people came into the enterprise and knew how to use enterprise software because they had been trained fully on the consumer side the average person spend an hour a day on Facebook they already know how these buttons work they know what to do what if we just brought that same technology in and helped them communicate and collaborate and work really well and yeah that experiment

Dan O’Leary: experiment has played out as you will all hear today and it was super fascinating to see not just what it was like to build enterprise software at a consumer company where no one really knew how to spell SAS or SSO or IDP or sock 2 things that I know what they mean and they mean a lot to our buyers and people I work with today but at a company that wasn’t used to doing that was focused on Farmville and cow clicking games it was a totally new thing so I remember yeah super interesting …

Dan O’Leary: but it really was fascinating I think most importantly to understand how organizations work and communicate and getting a front row seat to some of the best companies and really understanding what makes them ick. that was one of my lasting takeaways from that experience.

Scott Smith: Yeah, one of the things that I think a lot about was just…

Scott Smith: how we went from a essentially non-existent organization or team to actually being, hundreds of people building a And I think a lot of that came as a result of products like Slack and other tools that were coming out at the time. Teams eventually came obviously before but I think one of the key takeaways for me was like we didn’t have as much of a villain. We just had an old way of doing things and some legacy enterprise SAS tools.

Scott Smith: And then when Slack came along it was like this boogeyman that we were all afraid of but we knew that we had to scale up otherwise we’re going to get beat. and…

Dan O’Leary: Yeah. …

Scott Smith: I think that happens a lot with all these SAS tools, right?

Dan O’Leary: Big time. and especially it’s the competition where you wake up every day and you’re like, ” Facebook is competing with Microsoft.” It’s like, that’s not uncommon in the consumer world. But all of a sudden, now it’s like in the enterprise world and it’s, Yammer and Teams versus Workplace and Work Chat. And you start to look at these partnerships as well as the competition very differently when I think we kind of expected a billion people would just kind of sign up for Facebook at work…

Dan O’Leary: because they already were familiar with it. And that didn’t happen. it’s actually a lot harder to drive change in the way people collaborate and communicate at scale. and a lot harder than just signing up for an account to share photos with your friends. Come to find out. A lot harder than anticipated.

Scott Smith: Yeah, abs.

Scott Smith: absolutely And I think even going back to your point about the CIO saying it’s hard to get people off Facebook. Ironically, getting them to work at and on a Facebook product in the workplace also had some it was like I don’t want to do that.

Scott Smith: I don’t mind scrolling through silliness, but I don’t want to become friends. That was another thing that was actually really interesting about Facebook is my co-workers would add me on Facebook and I had just met them in a meeting and I probably didn’t ever see them again. So lots of different enterprise social stuff. I don’t know.  You have how many of your teammates are your friends on Facebook?

00:05:00

Dan O’Leary: Yeah, personally,…

Dan O’Leary: for me it’s a little different. And since I’ve been at Box, I’ve been in three or four people’s weddings, live on the same street as some of my dear friends. So, I’ve experienced that firsthand. But you’re right, sometimes you just want to go to work, you want to connect maybe over an affinity group or community, but you’re like, I’m not ready to find out everything about these people and their dogs and their baking habits. I just, happy to know them as an acquaintance. And that a lot of those modalities just didn’t necessarily translate as expected, but others did.

Dan O’Leary: And I think I have so many good stories of people who were able to make connections, build community, find job opportunities, like using the technology in ways that we had certainly never anticipated and you couldn’t have…

Dan O’Leary: because each leader just had a slightly different way of working and communicating and it was super fascinating to see all the different permutations as that spanned out across the globe. Yeah.

Scott Smith: I think another interesting thing that I always think about is pro products like box or…

Scott Smith: zite in my case but there’s so many different tools that came about because somebody was at work and they were frustrated with how their current workflow was developing and I think about even a Facebook, it’s like how were we communicating? we started off by making a Facebook group and…

Scott Smith: it was like a crazy experiment experience and then you’d have hundreds of Facebook groups.

Dan O’Leary: Yeah. Yeah.

Scott Smith: And then eventually it’s a sort of product market fit pull thing. that brings you back to why you’re here, which is a couple different questions I have to start with. When I got to know you had just been at Box for a few years. Was it three, four, something like that? yeah.

Dan O’Leary: Good tour, Four years. I’m back. So, it’s great. boomerangs. Yeah.

Scott Smith: So, I would love to know what’s it like being one of those what do they call it? Boomerang kind of. Yeah. Yeah. what’s that Is it like you come home, you go back to work? how does that feel?

Dan O’Leary: Yeah. It’s like marrying the same person twice, I suppose. so, you’re getting into, but also what’s the proverb about the the river is never the same on two days. things are always changing in business.

Dan O’Leary: So the company I returned to was fundamentally different than the one I left. And it’s really important I think for anyone that’s listening to this, you don’t really go back to anything. You just go forward with maybe the same employee ID or in my case email and I return to spam that I had forgotten I signed up where from VMware or something like gosh got to delete that out. it was great because you come back in with an established network and some things about the product and company but at the same time you’re a different person. The market’s different.  the opportunity is different and what I saw the opportunity I saw is now the one we’re realizing is that the opportunity for partners at Box it was underdeveloped and we really needed people that were incredibly passionate about how to scale our business with and through partners that I think u Meta is world class at. So it was a really great opportunity for me to leverage that experience and now start to take a lot of the things that you and I worked on and now scaling it in a different type of company focused on content AI.

Dan O’Leary: We’re in similar world worlds here,…

Dan O’Leary: but very fundamentally different than returning to something. You’re just going forward in a more familiar way. I don’t know, a reboot. J.J. Abrams would be happy with the way boomerangs work. I think start throwing punches and…

Scott Smith: At I don’t know did you have to prove yourself on day one…

Scott Smith: because you had been there you left maybe people felt like you had abandoned them and you wanted to show how amazing you are like you bring a strong passion game Max yeah exactly did you go after Aaron.

Dan O’Leary: find the biggest guy take him out

Scott Smith: What was that like?

Dan O’Leary: No, it was surprising. I actually felt very welcomed.

Dan O’Leary: They had made stickers of me and handed them out to some people and those still exist somewhere and it was fascinating to start to understand what was different and then my role was different. I had left leading parts of our technical services team working in solution architecture and I returned doing a growth and strategy and partnerships role. So just fundamentally different role based on learning how to scale these businesses up and build better partnerships.  So it was also like I was in different rooms working with different people. I think one of my biggest observations having spent years focused on Box the product putting many of our largest customers on box GE is probably one of my favorite projects.

Dan O’Leary: What I’ve been focused on is more box the company and it’s a lot harder to fix a company than it is a product or to build things with people and align road maps and teams and do internal partnerships substantially harder than working on a client project or…

Dan O’Leary: a go live even when it’s for hundreds of thousands of people and it’s just been a continued area of humility and growth for me over the past few years.

Scott Smith: you’ve used the word a bunch of times I think in the context of Facebook and…

00:10:00

Scott Smith: box partnerships I feel like when I came from a company called dine to pars to Facebook and I typically really only thought about things in terms of customers not so much partners like it it seems like you’ve made and…

Scott Smith: I think Facebook and our bosses at Facebook often talked about partnerships it’s clearly a different thing right customer versus partnership how do you view it what’s the big difference for you obviously you’re spending a lot of time there  Okay.

Dan O’Leary: Yeah. Yeah.

Dan O’Leary: So to me a partner is just a customer disguise like hey I got you because that partner represents many of your customers and prospects. They are the ones that are probably in that office every day. They’ve sold Salesforce, Service Now, They understand the lines of businesses. They understand how people work. And those partners are so key in helping customers get value from the tools and services and solutions you build. So I think early on when I was working in professional services and then throughout my career, I’ve always seen the value of partners who can help, build in and around your product, make your customers super happy and successful.

Dan O’Leary: And the more they do that, the more their business grows and the more value you create in that partnership. those folks work when you don’t. you’re on the beach, they’re out selling for you, they’re out delivering for you. And when you have a mindset that is based on both customer success and I think partner success, really great things can happen. And I think a lot of,…

Dan O’Leary: revenue leaders may think that Partnerships are a strategy. And they’re a strategy to grow. And it’s really a strategy not just about growing your business, but growing the success of your customers by aligning them and working with the right partners.

Scott Smith: this kind of focus on ensuring customer success,…

Scott Smith: partner success, what was that I mean did you have a sense for that before box? I think I’m trying to remember your career path where did you go right after college

Dan O’Leary: Yeah, I went to work at a company called Laserfish, which is still around and still exists. And I had a chance to work with partners there. And they only worked and fulfilled with partners. And don’t let the lack of gray hair fool I keep it tight. But this was in the early 2000s and we were physically shipping software. you’d go down to the store room and you’d put stuff in a box and you’d shrink wrap it. You’d mail it to a customer, you’d mail it to a partner. and when you understand that this is just a path to market. The same way let’s say some companies will only buy from a vendor direct. Some are going to buy through a marketplace and they buy through CDW. Maybe they’ll buy through some type of partner and others will only buy through a partner. They only work with those types of companies.

Dan O’Leary: To me, it’s just a different path to market than maybe the traditional SAS playbook has had where partnerships, especially I think historically, maybe they weren’t as valuable or outside of tech partnerships, there’s a difference between writing code, but if you want to get on a sales call and sell something or deploy something together, …

Dan O’Leary: a lot of the value prop of software as a service was that things were easy. back to workplace, you don’t need training on it. We’ve already trained A billion people already know how to use this product. So what’s the role then of a partner in that world? And I think that is especially now with AI just like roaring. It’s really something that’s going to have to be redefined again just as much as the playbook now is different than the one probably 5 years ago.

Scott Smith: Yeah. I think a great example of this dynamic of it should be self-s serve and…

Dan O’Leary: yeah.

Scott Smith: in reality it’s not like you think about Scott Dan setting up these demo accounts for our customers at workplace and prefabricfilling every imaginable piece of CRM content like making a hundred groups adding descriptions and banners and headlines and all these kind of things which is actually really cool and I think it was a great strategy that we developed and practiced well before anything was automated. and I think even with the AI, it’s like we’re also excited about the direction it’s going, but we still have a ways like I watch a lot of Erin’s tweets and…

Scott Smith: video examples about what AI can do. And to me he’s so far ahead of everyone else, he’s kind of like beast mode in that category for sure.

Dan O’Leary: Yeah.

Dan O’Leary: And I think there’s those of us who are practitioners the rate of change is just so insane outside of our companies it’s so hard to stay on the cutting edge. And I think that’s where I’m like hey Slalom has 6,000 people who are AI certified. Floyd has 10 times as many when we’re trying to drive outcomes for a customer around data and AI. I’m I’m an expert on content and…

Dan O’Leary: I’m not an expert on everything really. I No one can be. And it’s changing so quickly. So I think in this AI driven world, the power of partnerships is going to become even more pronounced because a lot of the things you need to make a customer successful can only come when you have that deep level of knowledge and expertise and sophistication that just vendors don’t.

00:15:00

Dan O’Leary: I wish everyone could, but no, not going to happen, guys. You’re going to need someone who understands you.

Scott Smith: Yeah. and…

Scott Smith: and more often than not, you need somebody on your team, you need a manager, leader, etc. you’ve gotten to work with some great leaders across, box, workplace, etc. what are some of the things that you’ve really, I don’t know, noticed or honed in on that create great teams? Because obviously terrible teams, bad teams. I’ve played on a few of them in sports.

Scott Smith: I’ve tried to avoid them professionally. my beer league hockey team is both terrible and fun. So …

Dan O’Leary: Yeah, that’s good.

Scott Smith: how do

Dan O’Leary: That’s the secret though is if you guys have fun together, even if you’re terrible, you’re still going to have good time. So, I think there’s part of it is enjoying the journey. I think one of the things like especially u in our tenure together, everyone was grinding so hard. We didn’t always take time to stop and smell the roses and enjoy it.

Dan O’Leary: And in hindsight, it’s really obvious that we’re doing amazing work with the greatest people and moving the needle every day. But when you’re in the thick of it, maybe that’s not always the case. Either way, I think in partnerships, in SAS, and in life, really it all comes back to communication and maybe that’s why, I’ve been married for a while. You too, Scott. It really is how you communicate effectively. understanding people’s objectives, working out loud, something we really advocated for with workplace is really key. And really, I think what you find is that the best teams and really the best leaders, they communicate they communicate with clarity and transparency and most importantly authenticity. And maybe that was one of my biggest learnings from workplace was the best leaders weren’t necessarily the ones who had the biggest personas.

Dan O’Leary: They were the folks who were the most authentic in their communications. And a good example of that was like, what’s his name? Tony from Air Asia, the CEO of Air Asia, going live while we were walking around campus on a tour. And he whips out his phone and…

Dan O’Leary: he starts going live in workplace to thousands of people at Air Asia. And Im one I’m like, ” my god, I don’t know if you’re supposed to be doing this here.” So I’m absolutely panicking. The other he’s like getting this immediate reaction from all of his airline teams all over the world. And he was a great example of a authentic and transparent communicator. And I think that to me was just a good example of it, but it all goes back to communication.

Scott Smith: Yeah, I think that’s such a great way to distill it.

Scott Smith: I think about some of the all hands we had at Facebook together where, you’d be sipping on your hot chocolate, sitting outside excited, and Zuck would come up and be like, “Hey everybody, we’re going to change the direction completely away to this.” And then five of his execs would go, “Yep, changing direction.” And it was like that’s what it was and that’s what it’s going to be from every single leader across the org for the next year.

Scott Smith: even if it sometimes felt like you were, little soccer players chasing the ball instead of playing strategically. I felt like that sometimes, but the message, the authenticity, and that consistency was pretty key there.

Dan O’Leary: Yeah. …

Dan O’Leary: totally. and then for organizations I think that are like us, everyone is going through a lot of change right now. Just the external world is changing so fast. The speed that you communicate and collaborate is really the speed that you can drive success within your organization.

Dan O’Leary: So if you’re stuck on analog processes or collaboration or sharing or comms that weak link now becomes as fast as you can go. And if you don’t remove those things, you’re never going to be able to keep up with the increasing demands of our customers and in the market. Just the speed you communicate and collaborate really drives a lot of success.

Scott Smith: So speaking of keeping up,…

Scott Smith: you mentioned this a little bit earlier, but there’s a lot of cutting edge stuff going on. I constantly feel like it’s actually pretty hard to keep up with the models, the features, these SAS tools that are going from zero to two million AR,…

Scott Smith: 100 million AR R. but I think one of the things that really stood out to me, so I actually attended Dan and Box Works event like ah yes.

Dan O’Leary: Yes, it worked.

Dan O’Leary: And because you were there, Scott, it was working. That was great. Thank you.

Scott Smith: But I think the thing that really was fascinating to me was how quickly this company took the ideas of, hey, AI is available. It can simplify, streamline,…

Scott Smith: make workflows easier, and they brought it into their product in a way that I didn’t feel like was overwhelming. And I think that’s one of the biggest things right now is as a practitioner, as somebody who’s obsessed and reading about and trying AI, there’s so much, but then for your customers, you need to make it simple and useful, right?  I think that seems to be the biggest thing in SAS.

Dan O’Leary: Yeah. …

Dan O’Leary: big time. And the same way we saw this at workplace, in order to be successful, you had to log in, you had to update your profile photo, you had to follow a couple co-workers.

Dan O’Leary: We came up with some simple steps that would get someone up and running and in a level of comfort. asking people to change the way they work is already really scary for most people. change is hard and if you don’t believe it’s hard to go try to change something in your own life and report back. Let me know Try to change the diet soda you drink. Let me know how that goes for you. Wow.

00:20:00

Scott Smith: There’s no way I’m going to touch that. I don’t know about you, So I was in New York over the weekend with my 12-year-old. I took her on a trip for her birthday and…

Dan O’Leary: Good for you. Amazing. It’s…

Scott Smith: the only place that I could find a diet Dr. Pepper was in the Met cafeteria. I literally looked everywhere and the one place was the most sophisticated place in the world, strangely.

Dan O’Leary: where you get it. accident there, folks. Dive Dr. Pepper drinkers, go to the Met. and that’s why it’s part change is hard and work changing the way you work is hard. I think when we’re thinking about how we’re going to bring AI to the masses, it’s all about meeting them where they’re at. So, no one cares about They care about what it can do for them. They care about how much faster they can make a decision or summarize a document or secure a piece of content or take you a lot of what we’re doing is extraction of content. So you take a giant contract or legal pleading or hundreds thousands of pages of documents and you need to just extract the key terms and information. by the way you need to be 100% accurate. You get a date wrong, you get a clause wrong, that has huge implications.

Dan O’Leary: So making those buttons look pretty and making the modals easy and making sure that it’s not a huge change in how people work so that they can enjoy their diet Dr. Pepper is really key and just continuing to iterate on that user feedback all the time. And yeah, I don’t know I feel you make it fun to use too. I think for me it’s when that a moment kicks in for somebody when they’re like my god this would have taken me two hours and I did it in 10 minutes.  you’re like, “Yes, and you can have that over and over and over and let me show you how.” So, it’s just helping people, I think, get comfortable in getting to that moment. So, then they want to do more and invest and work a little more and then AI can actually become valuable for them. But one cares if you’re not bringing something they care about.

Scott Smith: Yeah, absolutely The moment is key. I frequently text my little sister a screenshot of a prompt that I used and it’ll be like, “Hey, go to this web page and…

Scott Smith: pull out the recipe so that I don’t have to deal with the, 18 page story.” And she’s like,…

Dan O’Leary: Yeah. Yes.

Scott Smith: that’s genius.

Dan O’Leary: His whole life story.

Dan O’Leary: Yeah. Yeah,…

Scott Smith: But I think my little sister’s this way.

Scott Smith: My wife she’s a school counselor at a middle school. her preferred and favorite thing right now is when she’s communicating with she speaks Spanish really well but she’s not so comfortable to do it over email. And it’s as simple as help me format and sort of adjust this email in another language. And she’s constantly raving about it. it’s this incredible thing. It is but it seems so simplistic to me.  But I think most people just need one core thing to come back to.

Dan O’Leary: Interestingly enough, that has proven to be the number one stickiest use case for general knowledge worker with box AI is that’s the one that they will come back to over and over and over.

Dan O’Leary: multinational who has a distributor in Quebec and you’re like that’s a different language than I speak but with AI you can now read and understand and work with that content which that is a use case I never even thought about because it doesn’t impact me that much and then you hear from your customers you’re like I use this 20 times a day like wow that is super powerful and that’s where you realize it’s not the real power isn’t in the technology it’s in how that changes the way that person and that team and then their customer partner whoever they’re collaborating with interact and I

Dan O’Leary: That’s something that maybe we got wrong with workplace is we thought the technology would be enough and…

Dan O’Leary: It’s really about the power and the productivity and what that actually means for a person.

Scott Smith: Yeah, I absolutely agree.

Scott Smith: At least for me personally, I think back to the obsession with customer feedback, talking to customers that I have now that I’ve sort of developed as CEO. I’m constantly excited, so, sort of like this crazy sine wave throughout the day. I’m kind of curious for you guys even for you, Dan, but how do you stay connected to the customer? I know some of your roles are like you’re talking to partners who are selling the product who are, it might be a couple steps, but how do you stay close? How do you make sure Something.

Dan O’Leary: Yeah, this goes back to Julian who was the head of workplace at the time. That guy I mean super Scott he was in the field on calls with customers making it happen from the front line.

Dan O’Leary: It was like watching a Roman commander on the front lines with his tor out and…

Scott Smith: Heat.

Dan O’Leary: it made you want to follow him because he was rushing in to combat every day harder than you were and you’re like this guy is absolutely nuts. Let’s do what he’s doing. And that has really rubbed off on me is I realized in order to be a good leader I cannot sit in a room and read slides or pontificate. I need to go get in the field, get on the call with a partner, get on the call with the customer, get in the room and talk to them. So it’s I mean for me every day multiple times a day I’m on calls with customers and partners and then there’s a few areas at Dreamforce we did almost 70 executive briefings in a bunch of those. So there’s just one after the other after the other and when you walk away you’re physically and mentally tired but you’re able to get so much feedback and have so many conversations one after the other. I think it’s really really critical now more than ever where you can read an AI summary of a meeting on Gong or something.

00:25:00

Dan O’Leary: No, no. You got to get in the room,…

Dan O’Leary: in three or four dimensions with a customer, with a partner, and talk to them and connect with them as a human being, and you’d be surprised how much better those outcomes will be. Yeah. I can’t recommend it enough.

Scott Smith: There’s been a few times over the last six months.

Scott Smith: One of the things that I’ve noticed is I have a product manager on my team. His name’s Finn and he’s very much like this go talk to a million people,…

Scott Smith: ping, LinkedIn, whatever. And he’s deep there. I’ve had other folks on my team who I’ll ask a question and they will copy verbatim the chat GBT response and I’m like dude first at least massage it a little bit but yeah…

Dan O’Leary: Yeah, right in your own voice.

Scott Smith: but I think this is that kind of like I can distill the customer versus I’m going to understand and…

Dan O’Leary: the same.

Scott Smith: talk to them is so critical and key I think if you try to create these little barriers between you and the  customer. I think I feel like occasionally we called him the missile because he was literally so focused. He was going right after the problem. He wasn’t afraid of it and I think that’s like my CEO thing is hire the best people, make sure we have money in the bank and then distill the vision and sort of be consistent with about it. But he was great at all those things. I loved working with that guy.

Dan O’Leary: He was I very rarely found people that I count can out outwork and…

Dan O’Leary: he is one of them. he was more endurance and more resilient and I respect that greatly. That’s exactly the type of leader personally that I like to follow is someone who I’m like yep they’re set an example that I’m going to always strive to have to reach myself.

Scott Smith: So re you’ve been married.

Scott Smith: I think you have a kiddo, one or…

Dan O’Leary: Two of them.

Scott Smith: Two of them.

Dan O’Leary: They’re young though. Scott, I got a little ways going to the vet with them. That’s for sure.

Scott Smith: Make sure you start feeding them diet Dr. Pepper now.

Dan O’Leary: Yeah. No.

Scott Smith: So hopefully that work, but the desire for excellence and the work ethic that you have combined with wanting to build a great family. I find it difficult. I’m not at all thoughtful about I mean I don’t think there’s a lot of this work life balance. I think that’s sort of a misnomer that you can’t actually ever get to. Julian would frequently say I don’t have work life balance and I’m okay with that. And I think that was actually pretty authentic.

Dan O’Leary: Yeah. I’m on my second sugar referral that I got.

Scott Smith: What’s your view on all that stuff?

Dan O’Leary: That’s how we do it. honestly, it’s a prioritization exercise and my family comes first because at the end of the day, no matter how much I love my work and my teammates, some of my best friends, etc. It’s really your family who are the ones that are most important to you. And I feel like in a partnerships role, if your most important partnerships, the ones with your family aren’t going like that’s very telling for me.

Dan O’Leary: So, it’s not that I have OKRs with my kids, it’s that I prioritize on the weekends, really try I keep my laptop locked up if I possibly can. You know what I mean? And same thing like if it’s Christmas break or something, just intentionally spending that time the same way. Yeah. If you’re a customer with a partner, you intentionally give them your time and attention and focus and you do that consistently.

Scott Smith: That’s awesome.

Dan O’Leary: Make them a priority. I don’t know. And little things too. so I run a lot now. I was telling before we hopped on, I just had a half marathon yesterday and my legs are a little sore and I run almost I’d say 95% of my miles are with the jogger. One or two kids at a time. It’s pretty good. Get a nice upper back workout. So, I ran I don’t know almost seven or 800 miles last year with my kids, both of them hours on end. It’s great. Get time with dad, run to the park, have a snack. So, I try to incorporate, I like, things that they like. and we do it together and it’s just a key part of how we work.

Dan O’Leary: But it’s like I love them the most and…

Dan O’Leary: my team knows My son has a badge for box when he comes to the office. He is well So yeah, I try to bring them around and other people get to know them too. So they’re part of our life now.

Scott Smith: I do find it a little more hard to believe that you don’t have family OKRs,…

Scott Smith: I imagine you taking your white out your wife out and being like, “All right, I’ve planned an executive retreat.

Dan O’Leary: I think I’ve definitely had them in the past.

Scott Smith: We’re going to spend two days thinking about the future together. Yep.

Dan O’Leary: And now mine are objective get the children to bed by 6:30 p.m. Key results, both children asleep by 7:00. You know what I mean? but a big part of it is just learning how to adapt your life. And at this season in our lives in particular, mine are very young and I don’t know, something I think about is they’re not going to want to hang out with me forever. Dad’s not going to be the coolest forever. And, is the time to check in.

Dan O’Leary: also say it is humbling to be an engaged parent and it actually I think makes me a lot better every day at what I do because I just start from a level of just sheer humility I’ve been punched in the face by this kid today like nothing that work what are you going to do to me I’ve had my co-workers that are 18 months and four poop on the floor and smack me it’s not going to phase me guys so that’s been a big part of it and then also I’ll say I don’t know if you felt the same way Scott that gentle parenting really helps me in tough meetings where I’m like What I want to say is one thing, but what I’m going to say is “Okay, honey, I’ve gotten a lot of practice where I think I used to be a lot more intense, maybe a lot more like I don’t know, aggressive. I’ve had to soften it a little bit because I have small children.” And then I show up at work with, ideally that same humility and gentle management style. Yeah, it’s not perfect, but it works.

00:30:00

Scott Smith: They also really help …

Scott Smith: how badly you communicate at all times. it’s like, “Dude, I told you that two minutes ago.” And then my wife will be with me and she’ll be like, “No, you didn’t.” And I’m like, ” okay. shoot. It’s terrible.

Dan O’Leary: Yeah, that’s something I think about often is that especially when I communicate to my team,…

Dan O’Leary: my partners, customers, I’m like, “Look, I’ve told you this six times. You may just now be starting to get it, but if my own crew, my own critters, they rely on me for everything and they don’t listen. So why would I expect my partner to listen if I told them once? So it actually I helped me understand that I need to communicate not just more clarity but through different modalities or different frequencies maybe it’s not just a slack maybe it’s a slack and an email maybe it’s a slack and an email and I walk around the block but they’re there honey let’s get down on your level and talk. So it really has made me conscious that I am not only a bad communicator but no one listens to me at all.

Scott Smith: Yes. I think that’s the other key takeaway of all leadership roles or…

Scott Smith: parental roles is nobody’s listening. So you just have to keep trying.

Dan O’Leary: Yep. Yeah.

Dan O’Leary: And keep making it interesting to them. it’s a big part. It’s like having built a communications platform, you really see this in action and…

Dan O’Leary: at scale. This is no joke.

Scott Smith: …

Scott Smith: Dan, so I have one final question for you so that you can, get back to running and the family and the building incredible future of the workplace.

Scott Smith: But, there are a lot of things. We’ve talked about a couple of them. all these kinds of things, but what are you really excited about personally, professionally over the next couple years? There’s so much going on. where’s your head at?

Dan O’Leary: Scott,…

Dan O’Leary: I hope that one day I can join you having some chickens. so I can eat,…

Dan O’Leary: a dozen eggs a day like Gaston. But if not,…

Scott Smith: Dude, there’s no eggs right now.

Scott Smith: It’s in the middle of the winter. It’s terrible. I have to buy them from Costco.

Dan O’Leary: no, no,…

Scott Smith: But sorry.

Dan O’Leary: no, no. Not at these egg fries, Scott. So, no, I think part of it is just, as you’ve done, I think you’ve set a great example.

Dan O’Leary: love coming on the pod and connecting and hearing other people’s stories. It’s continuing to just share and enjoy the time. I think I really want to be a more resilient leader and enjoy the journey a little bit. And then when I look back at what I’ve accomplished, what I want to do is help companies and people, my partners really achieve their potential.  I think I’m starting to define a lot of my success now based on the success of others, my partners, etc. And making that the goal, rather than just, a number, a dashboard or something, I think, cuz that that’s never going to end. That’s going to be an area of continuous improvement. I don’t know. And some point I want to buy a power washing business or something like I really enjoy enterprise software, but some days do I just want to go like paint rain gutters in the neighborhood or buy a wood chipper.

Dan O’Leary: So hopefully when I’m ready to be put out to pasture, I’ll be stump grinding or doing something pretty dirty with my hands. that’s the long-term plan.

Scott Smith: Dude, you chose some of the most hardcore ones.

Scott Smith: Stump grinding, wood chipping, paint. my gosh.

Dan O’Leary: Yeah. No,…

Scott Smith: Some of my favorite things to do are build stuff in my backyard. I just built this massive play structure for my kids slowly over many weeks and I suck at everything, but it’s been fun to do. All right, hey, it’s so great to have you and thanks thanks for spending some time with us.

Dan O’Leary: thank you, Scott. And team, let’s connect and let’s keep the conversation on going.